Vacation rentals with a kayak in Southside

Find and book unique kayak rentals on Airbnb

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Popular amenities for Southside kayak rentals

House rentals with a kayak

Guest favorite

Home in Cruz Bay

5 out of 5 average rating, 9 reviews

Pirates Villa-Family Friendly, Beach Access, Kayak

JayRating, 5 stars9 months ago
Everything was advertised, was worried with this being a condo and possible loud neighbors, not the case. Beautiful house and accommodations
Guest favorite

Home in Northside

4.8 out of 5 average rating, 172 reviews

PANOrama! Standalone Home 3 KNG bd AC WiFi EZPkng

ShaneRating, 5 stars2 weeks ago
Great place. Lots of room. Can’t put a price on the view. Brand new washer and dryer. Huge living room. Bedrooms are good size with great mattresses. You can’t do better than this place
Guest favorite

Home in Cruz Bay

4.91 out of 5 average rating, 23 reviews

Pond Bay Paradise-Ocean Views, Beach w/ Kayaks & S

NickiRating, 5 stars2 months ago
Beautiful place with a beautiful view. Almost everything you need it was there. Loved having a greeter to meet us and then show us how to get to the place. Only lost power twice, once for two hours the other was right before we left. Company was very responsive when we messaged them to let us know it wouldn’t last and if we had problems to message them again. The outside shower wasn’t working due to the salt air. They were by within five minutes of my call and got it working. Just can’t say enough about the beauty of the area end of the home and the great customer service. I loved seeing the sunrise every morning the chickens in the neighborhood and the deer. The stars at night were amazing. I hope we will be back in very near future.
Guest favorite

Home in Cruz Bay

5 out of 5 average rating, 15 reviews

Castaways Villa- Steps from the Beach, Kayaks, SUP

DonnaRating, 5 stars8 months ago
We had the best stay. Brandon and team always reached out to see how they could help to make sure our trip was perfect from beginning to end. Loved the location and nice to have a little private beach all our own. Easy to get into Cruz Bay for restaurants, shopping etc. The house had everything that we could have wanted. Felt right at home. Thank you Brandon and staff.
Guest favorite

Home in Cruz Bay

5 out of 5 average rating, 11 reviews

Southern Star- Kayaks & SUPS, Steps to Beach, Ocea

erinRating, 5 stars9 months ago
The place was exactly as advertised. Very comfortable for our group of 4 adults and a five year old. Spacious rooms afforded upstairs and downstairs privacy with short walk around the driveway to the beach. Our last night was saw 3 deer walk across the property and feed right behind the house. Lovely decks and patios. Easy to get to close market and town. Brandon and his team were excellent hosts. We would definitely stay here again and highly recommend this place.
Guest favorite

Home in EAST END

4.95 out of 5 average rating, 64 reviews

Private Pool in Paradise w/Ocean View! King+BBQ

VeronicaRating, 5 stars5 days ago
First time on the island and we loved every part of it, Brian’s place was a quick walk to Saphire beach, which has a beautiful beach bar. We absolutely loved the water at sapphire and coki beach! Make Sure you get kishawn’s and Bernadette’s info from Brian for your cab services! They were absolutely amazing and knew the best places for anything you needed. The air bnb was clean, the ac was great, and Brian answered very fast for any needs! I absolutely be going back and using Brian’s place again.

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